Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
  • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
  • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
  • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
  • C07D231/18—One oxygen or sulfur atom
  • C07D231/20—One oxygen atom attached in position 3 or 5
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
  • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles

Definitions

• the present invention relates to certain new pyrazole derivatives, a process for their preparation and their use as herbicides.
• Japanese Publication No. Sho 54-36648 published prior to the filing date of the present application discloses that the compounds of the general formula in which R 1 represents a hydrogen atom or a lower alkyl group, R 2 represents a lower alkyl group, and X represents a halogen atom or a nitro, lower alkyl, trifluoromethyl, lower alkoxy, lower alkanesulfonyl -, Cyano, lower alkylthio or aliphatic acyl group, n is 1, 2, 3 or 4 and, - if n is 2, 3 or 4, the radicals X may be the same or different and Y is an oxygen Atom or a sulfur atom, and their salts or their esters with an organic acid selected from aliphatic, alicyclic or aromatic carbon acids, carbamic acids, sulfonic acids, thiophosphoric acid, diesters, carbonic acid or thiocarbonic acid monoesters, dibasic acids and esters with organic acids of the general formula in which R 10
• R represents a halogen atom or an aryl group which is optionally substituted by halogen or a C 1 - to C 6 -alkyl.
• the present invention also encompasses a process for the preparation of a pyrazole derivative of the formula (I), in which 1,3-dimethyl-4- (2,4-dichlorobenzoyl) -5-hydroxy-pyrazole with an acid halide of the general formula is implemented in which X and R have the meanings given above and Hal represents a halogen atom.
• the new pyrazole derivatives of formula (I) of the present invention have been found to have excellent herbicidal activity. Furthermore, the compounds of the present invention show an excellent herbicidal action even at low doses in comparison to the compounds known from the prior art. In addition, it has been found that the compounds of the present invention are well tolerated by crop plants so that they are safe to use. The present invention thus embodies significant technical progress.
• Preferred compounds according to the present invention and preferred starting materials of the formula (II) are those in which X for halogen atoms such as fluorine, chlorine, bromine or iodine atoms and R for halogen atom such as the aforementioned or an aryl Group such as phenyl or naphthyl, optionally substituted by a halogen atom such as the aforementioned or a C 1 -C 6 -alkyl group such as methyl, ethyl, propyl, isopropyl or n-, iso-, sec- or tert- Stand butyl.
• X for halogen atoms such as fluorine, chlorine, bromine or iodine atoms
• R for halogen atom such as the aforementioned or an aryl Group such as phenyl or naphthyl, optionally substituted by a halogen atom such as the aforementioned or a C 1 -C 6 -alkyl
• Particularly preferred compounds and starting materials are those in which X represents chlorine atoms and those in which R represents a chlorine atom or phenyl, naphthyl, monochloro-substituted phenyl or o-, m- or p-tolyl.
• a very particularly preferred compound is the compound in which X and R both represent chlorine atoms.
• Examples of preferred acid halides of the general formula (II) for use as starting material in the process of the present invention are the following: 3,3-dichloro-2-phenyl-acrylic acid chloride, 3,3-dichloro-2-p-tolylacryloyl chloride, 3 , 3-dichloro-2-m-tolylacryl chloride, 3,3-dichloro-2-o-tolylacryl chloride, 3,3-dichloro-2-p-chlorophenylacryl chloride, 3,3-dichloro-2- ⁇ -naphthylacryl chloride , Trichloroacrylic acid chloride and in addition to these the other corresponding halides, preferably the bromides.
• suitable solvents or diluents for use in accordance with the present invention: water, aliphatic, cycloaliphatic and aromatic hydrocarbons, which may in any case be chlorinated (for example hexane, cyclohexane, petroleum ether, ligroin, benzene, toluene, Xylene, methylene chloride, chloroform, carbon tetrachloride, ethylene chloride, trichloroethylene and chlorobenzene), ethers (e.g.
• dimethyl ether dimethyl ether, methyl ethyl ether, di-isopropyl ether, dibutyl ether, propylene oxide, dioxane and tetrahydrofuran
• ketones e.g. acetone, methyl ethyl ketone, methyl isoproputyl ketone and) Acetonitrile, propionitrile and acrylonitrile
• esters e.g. ethyl acetate and amyl acetate
• acid amides e.g. dimethylformamide and dimethylacetamide
• sulfones sulfoxides (e.g. dimethyl sulfoxide), sulfolane and bases (e.g. pyridine).
• the process of the present invention can be carried out in the presence of an acid binding agent such as a hydroxide of an alkali metal, a carbonate, a bicarbonate, an alcoholate, a tertiary amine (e.g. triethylamine), diethylaniline or pyridine.
• an acid binding agent such as a hydroxide of an alkali metal, a carbonate, a bicarbonate, an alcoholate, a tertiary amine (e.g. triethylamine), diethylaniline or pyridine.
• the process of the present invention can be carried out over a wide temperature range, for example at a temperature between -20 ° C and the boiling point of the reaction mixture, and preferably at a temperature between 0 ° C and 100 ° C.
• the reaction is preferably carried out at atmospheric pressure, but can also be carried out under reduced or elevated pressure.
• the active compounds according to the invention influence plant growth and can therefore, will be used to destroying broad-leaved plants, germination-inhibiting agents and in particular as herbicides as E ntlaubungsstoff, desiccants. "Weeds" in the broadest sense mean plants that grow in places where they are not wanted.
• the active compounds according to the present invention can be used, for example, to control the following plants: Dicotyledon weeds of the Genera Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsaus, Rotalo, Carduus, Carduus , Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea and Solanum; and
• the active compounds according to the present invention can be used, for example, as selective herbicides in the following crops: Dicotyledon cultures of Genera Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis and Cucubirta; and
• the compounds can be used for total weed control, for example on industrial sites and railway bodies and on paths and squares with or without trees.
• the compounds for weed control in perennial crops for example afforestation, ornamental tree plantations, orchards, vineyards and gardens, citrus forests, walnut plantations, banana plantations, coffee plantations, tea plantations, rubber plantations, oil palm plantations, cocoa plantations, soft fruit plantations and hop crops are used in crops and crops of the year as well as in hop crops and crops .
• the active ingredients can be converted into the usual formulations, such as solutions, emulsions, suspensions, powders, dusts, foams, pastes, soluble powders, granules, aerosols, suspension emulsion concentrates, natural and synthetic materials impregnated with the active ingredient, very fine capsules polymeric substances, and formulations for ULV (ultra-low-volume) cold and warm nebulization.
• solutions such as solutions, emulsions, suspensions, powders, dusts, foams, pastes, soluble powders, granules, aerosols, suspension emulsion concentrates, natural and synthetic materials impregnated with the active ingredient, very fine capsules polymeric substances, and formulations for ULV (ultra-low-volume) cold and warm nebulization.
• preparations can be prepared in a known manner, for example by mixing the active substances with extenders, i.e. liquid or solid diluents or carriers, optionally using surfactants, i.e. Emulsifiers and / or dispersants and / or foam-forming agents.
• extenders i.e. liquid or solid diluents or carriers
• surfactants i.e. Emulsifiers and / or dispersants and / or foam-forming agents.
• organic solvents can also be used as auxiliary solvents, for example.
• Aromatic hydrocarbons such as xylene, toluene or alkylnaphthalenes, chlorinated aromatic or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic or alicyclic hydrocarbons such as cyclohexane or paraffins, for example mineral oil fractions, alcohols such as buthanol, are mainly suitable as liquid diluents or carriers, in particular as solvents or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, or strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
• chlorinated aromatic or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride
• aliphatic or alicyclic hydrocarbons such as cyclo
• Ground natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals such as highly disperse silica, aluminum oxide and silicates can be used as solid carriers.
• Crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite as well as synthetic granules of inorganic and orga can be used as solid carriers for granules African flours and granules made from organic material such as sawdust, coconut shells, corn cobs and tobacco stalks are used.
• Nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and hydrolysis products of albumins can be used as emulsifiers and / or foaming agents.
• Dispersants include, for example, lignin sulfite leaching and methyl cellulose.
• Adhesives such as carboxymethyl cellulose and natural and synthetic polymers in the form of powder, granules or latices such as gum arabic, polyvinyl alcohol and polyvinyl acetate can be used in the preparations.
• colorants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian blue, and organic dyes such as alizarin dyes, azo dyes or metal phthalocyanine dyes, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc use.
• inorganic pigments for example iron oxide, titanium oxide and Prussian blue
• organic dyes such as alizarin dyes, azo dyes or metal phthalocyanine dyes
• trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc use.
• the preparations generally contain 0.001 to 100% by weight, preferably 0.05 to 95% by weight, of the active substance,
• the active compounds according to the invention can be used in the formulations or in the various use forms in a mixture with other active compounds, such as fungicides, bactericides, insecticides, nematicides, herbicides, bird repellants, growth factors, plants nutrients and agents to improve the soil structure.
• the active ingredients can be used as such, in the form of their preparations or as use forms prepared therefrom, e.g. as ready-to-use solutions, emulsions, suspensions, powders, pastes and granules. They can be applied in the usual way, for example by spraying, dusting, dusting, scattering and watering.
• the active substances can also be incorporated into the soil.
• the content of active ingredients in the various formulations mentioned or ready-to-use preparations is generally from 0.01 to 95% by weight, preferably from 0.05 to 60% by weight.
• the amount of active ingredient to be used can be varied within a substantial range. It essentially depends on the type of effect desired. In general, amounts of the active ingredient between 0.1 and 2.0 kg / ha, preferably between 0.25 and 2 kg / ha, are used.
• the present invention also encompasses herbicidal compositions comprising, as active ingredient, a compound according to the present invention in admixture with a solid or liquid diluent or carrier or in admixture with a liquid surfactant-containing diluent or carrier included.
• the present invention further comprises a weed control method, which is characterized in that a compound according to the present invention, alone or in the form of a composition comprising an active compound as a compound of the present invention in admixture with a diluent or Carrier contains, applies.
• the present invention is also directed to crop plants which are protected against weed damage by being grown on areas on which a compound according to the present invention, alone or in admixture with one, immediately before and / or during the time of cultivation Diluents or carriers have been applied.
• compositions according to the invention and the herbicidal activity of the compounds of the present invention are illustrated by the following examples.
• the compounds according to the invention are each designated by the number (in parentheses) of the corresponding preparation example. Parts and ratios are based on weight.
• the known comparison compounds are defined as follows: (a compound disclosed in JP-AS 36648/79); (a compound disclosed in JP-AS 36648/79).
• a wettable powder was prepared by grinding and mixing 15 parts of compound (1), 80 parts of a mixture consisting of powdery diatomaceous earth and powdery clay (1: 5), .2 parts of sodium alkylbenzenesulfonate and 3 parts of a condensate of sodium Alkyl naphthalene sulfonate and formalin are produced. This was diluted with water before spraying.
• An emulsion was prepared by mixing and stirring 15 parts of compound (2), 70 parts of xylene, 8 parts of polyoxyethylene alkylphenyl ether and 7 parts of calcium Alkylbenzenesulfonate produced. This was diluted with water before spraying.
• a powder for use as a dusting agent was prepared by grinding and mixing 2 parts of the compound (3) and 98 parts of clay powder.
• a powder for use as a dusting agent was prepared by grinding and mixing 1.5 parts of the compound (4), 0.5 part of isopropyl hydrogen phosphate (PAP) and 98 parts of clay powder.
• Granules were prepared by adding 25 parts of water to a mixture consisting of 10 parts of the compound (5), 30 parts of bentonite (montmorillonite), 58 parts of talc and 2 parts of lignin sulfonate, kneading and granulating by means of an extruder granulator, thereby producing a granulate with a grain size of 0.43 to 2.00 mm (10 to 40 mesh) was obtained, which was dried at 40 ° C to 50 ° C. The granules obtained were applied by scattering.
• a granulate was produced by charging a rotary mixer with 75 parts of a mineral granulate with a particle size distribution of 0.2 to 2 mm, spraying on 7 parts of the compound (7) dissolved in one organic solvent on the granules while rotating the mixer so that the granules were moistened homogeneously and drying at 40 ° C to 50 ° C.
• the granules obtained were applied by scattering.
• Emulsifier 1 part by weight of benzyloxy polyglycol ether.
• An active ingredient preparation in the form of an emulsifiable concentrate was obtained by mixing a part by weight of the active ingredient with the abovementioned amounts of the solvent and the emulsifier. A predetermined amount of the preparation was obtained by diluting with water.
• the pots were watered up filled to a depth of about 6 cm, and a predetermined amount of the active ingredient in the form of an emulsion was added to the water by means of a pipette.
• the water in the pots was let out at a rate of 2 cm / day within 2 days of treatment. 4 weeks after the treatment, the herbicidal activity and the degree of phytotoxicity were evaluated on a scale from 0 to 10 on the following scale.

Landscapes

• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Life Sciences & Earth Sciences (AREA)
• Agronomy & Crop Science (AREA)
• Pest Control & Pesticides (AREA)
• Plant Pathology (AREA)
• Health & Medical Sciences (AREA)
• Engineering & Computer Science (AREA)
• Dentistry (AREA)
• General Health & Medical Sciences (AREA)
• Wood Science & Technology (AREA)
• Zoology (AREA)
• Environmental Sciences (AREA)
• Agricultural Chemicals And Associated Chemicals (AREA)
• Plural Heterocyclic Compounds (AREA)

Applications Claiming Priority (2)

Publications (2)

Family

ID=13932357

Family Applications (1)

Country Status (12)

Families Citing this family (1)

Family Cites Families (4)

• 1981
  • 1981-06-10 JP JP56088062A patent/JPS57203069A/ja active Pending
• 1982
  • 1982-05-14 PH PH27304A patent/PH18593A/en unknown
  • 1982-05-27 US US06/382,750 patent/US4431441A/en not_active Expired - Fee Related
  • 1982-06-01 PT PT74983A patent/PT74983B/pt unknown
  • 1982-06-01 EP EP82104776A patent/EP0067981A3/fr not_active Withdrawn
  • 1982-06-07 IL IL65990A patent/IL65990A0/xx unknown
  • 1982-06-08 CA CA000404702A patent/CA1176262A/fr not_active Expired
  • 1982-06-09 TR TR21308A patent/TR21308A/xx unknown
  • 1982-06-09 AU AU84700/82A patent/AU8470082A/en not_active Abandoned
  • 1982-06-09 BR BR8203415A patent/BR8203415A/pt unknown
  • 1982-06-09 ES ES512963A patent/ES8304089A1/es not_active Expired
  • 1982-06-10 KR KR1019820002594A patent/KR840000502A/ko not_active Withdrawn

Also Published As

Similar Documents

Legal Events